JPH0399059A - 4-alkoxy-and 4-(substituted) aminoaryl pyrpolinone derivatives - Google Patents

Abstract

NEW MATERIAL: Compounds of formula I [X, Y are H, halogen, alkyl, alkoxy, aryloxy or the like; Z is halogen, alkyl or alkoxy; n is 0-3; A is alkyl, alkenyl alkynyl, cycloalkyl, aryl, phenoxy or the like; B is OH, alkoxy, cycloalkoxy, or formula II (C, D are H, alkyl, alkenyl, cycloalkyl, phenyl, hetaryl, or 3-9 membered ring with bond N.].

EXAMPLE: 3-(3-Trifluoromethylphenyl)-1-isopropyl-pyrrolidin-2,4-dione.

USE: Herbicide.

PROCESS: For example, intramolecular condensation of N-acylamino acid ester of formula II (R¹ is alkyl), is performed in the presence of diluent, and base, to obtain the compound of formula I in which B is OH.

COPYRIGHT: (C)1991,JPO

Description

[Detailed description of the invention]

The present invention relates to new 4-alkoxy and 4-(substituted)amino-3-arylvirolinone derivatives, a process for their preparation and new intermediates for said process, and their use as herbicides. It is something. The pharmaceutical properties of 3-acylupilysine-2,4-diones have already been described (S. Suzuki
) and others, Chemical & 7Arceutical Bulletin (Chew. Pharm. Bull.), ■
5, l l 20 (1 967)). N-7 enylubi-lysine-2,4-diones are further synthesized by R. Schmierer and H. Mildenberger, Liebigs Ann. C.
bem. ), 1985, 1095. The biological activity of these compounds has not been described. Compounds with similar structure (3-aryruvirolidine-2
．． 4-Sions) Haeureurope Ao, 262, 39
9, but the herbicidal activity of these compounds is not disclosed. 3-allyl pyrrolidine-2,4-dione derivatives which have insecticidal, acaricidal and herbicidal activity and can contain a hydroxyl in the 4-position of virolinon have been described before the filing of this application. Unannounced January 7, 1989
The compounds which are also described in the German patent application P3 900 301.9 of the same name and named by name are excluded from the scope of protection of the present application by disclaimer of patent rights. General formula (1) [wherein X and Y independently represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, or in each case unsubstituted or substituted aryloxy or arylthio, 2 is halogen, represents alkyl or alkoxy, n represents the number 0, l, 2 or 3; A is in each case unsubstituted or in each case halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl; , cycloalkyl optionally interrupted by heteroatoms, unsubstituted or halogen,
represents arylalkyl substituted by alkyl, halogenoalkyl, alkoxy and/or nitro, or unsubstituted or substituted aryl, in which the possible substituents are halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or each phenoxy or phenylthio, in each case unsubstituted or substituted by halogen, alkyl, alkoxy, halogenoalkyl and/or halogenoalkoxy; B represents hydroxyl, alkoxy, halogenoalkoxy or cycloalkoxy, the ncroalkyl group being unsubstituted; or substituted by halogen and/or alkyl, or C/B represents a group N, where \D C and D are, independently of each other, hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or represents polyalkoxyalkyl, cycloalkyl optionally interrupted by a heta atom, or in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl, or and D together with the nitrogen atom to which they are attached form an optionally substituted ring which may be interrupted by 3- to 9-member optionally other heteroatoms; , with the proviso that if B represents hydroxyl and A has a meaning other than optionally substituted aryl, at least one group X, Y or 2 does not represent chlorine or methyl] 4-alkoxy and 4-(substituted) amino-3-arylvirolinone derivatives have now been found. Aliphatic carbon chains, such as alkyl, halogenoalkyl, arylalkyl or phenoxyalkyl, are in each case straight or branched. In substituted systems, for example substituted alkyl, alkenyl, cycloalkyl or aryl, the substitution is in each case carried out by one or more identical or different substituents. Aromatic systems are preferably substituted with 1 to 5, especially 1 to 3, substituents, and cyclic systems are preferably substituted with 1 to 3 substituents.
Substituted with ~8, especially l~5 substituents. Furthermore, compounds of the formula (I) in which a) B represents hydroxyl and the radicals A1X, Y and Zn have the meanings given above are provided,
n) [wherein A%X, Y, Z and n have the above meanings, and R
1 represents alkyl, in particular methyl or ethyl], or b) B is alkoxy, Compounds of formula (I) representing halogenoalkoxy or cycloalkoxy, the cycloalkyl group being unsubstituted or substituted by halogen and/or alkyl, and A1X% Y, Z and n having the abovementioned meanings is a compound of formula (I) in which B represents hydroxyl, optionally in the presence of a diluent and optionally in the presence of an acid-binding agent, to form a compound of formula (III) R2-x' (DI)E, where R2 is alkyl, represents halogenoalkyl or cycloalkyl, the cycloalkyl group being unsubstituted or substituted by halogen and/or alkyl, and x1 represents halogen or another radical common for alkylating reagents] or c) a compound of formula (I) in which B represents N and \D ASC, D, X, Y%2 and n have the meanings given above, Formula (I) in which B represents hydroxyl
) with amines of the formula (IV) C/HN (■)\D, where C and D have the meanings given above, optionally in the presence of a diluent and optionally a dehydrating agent. I also found something to do. It has also been found that new 4-alkoxy and 4-(substituted) amino-3-arylvirolinone derivatives of general formula (1) have herbicidal properties after jTh. Surprisingly, the 4-alkoxy and 4-(substituted)amino-3-arylpyrrolinone derivatives of general formula (I) according to the invention exhibit pronounced herbicidal activity and at the same time excellent resistance to important crop plants. show. Preferred compounds of formula (I) are those in which X and Y are independently of each other hydrogen, fluorine, chlorine, bromine, iodine, CI-C. -Alkyl, C I- C I-
represents alkoxy, halogenoC,-C,-alkyl or in each case unsubstituted or substituted with 1 to 5 identical or different substituents, 7enoxy or 7enylthio, the substituents selected for 7enyl being fluorine,
Chlorine, bromine, iodine, C. -C, -alkyl, C, -C
, -alkoxy and hihalogen-C, -C. -alkyl, and Z is fluorine, chlorine, bromine, iodine, C, -C, -
Alkynore represents C, -C, -anolekoxy, n represents the number 0.1, 2 or 3, and A is in each case unsubstituted or in each case halogen-substituted C I"-C I !-Alkyl, C, -C
,-alkenyl, CsCa-alkynyl, C1C 1G
-Alkoxy C2-C. -Alkyl, Cl? ．．
-Polyalkoxy C. -C. -alkyl or C,
-C. . -alkylthio C,-C,-alkyl or cycloalkyl having 3 to 8 ring atoms, which may be interrupted by oxygen, nitrogen and/or sulfur, or A is in each case not It phenyl-C I-C a-alkyl, 7-enyl or naphthyl substituted on the phenyl moiety by 1 to 5 identical or different substituents, the substituents selected in each case being fluorine, chlorine, bromine; , iodine, C I-C
a-alkyl, C I- C a-alkoxy, nor\rogeno C + - C s-alkyl, halogeno C
t-C*-alkoxy or in each case unsubstituted or fluorine, chlorine, bromine, iodine, CIC4-alkyl, CrCh-alkoxy, halogenoC■-C4
-alkyl and phenoxy or phenylthio selected from the group consisting of halogeno C, -C, -alkoxy and substituted by f-1 to 5 identical or different substituents, B is hydroxyl, c, -C+. -alkoxy, nologenoC, 1C,. -alkoxy or cycloalkoxy having 3 to 7 ring atoms, the cycloalkyl group being unsubstituted or fluorine, chlorine, bromine and CI
substituted by 1 to 5 identical or different substituents from the group consisting of -C,-alkyl or C/B represents a group N, in which \D C and D independently of each other are hydrogen , CICIO-alkyl, C, -C,. -alkenyl, C, -Ca-
Alkoxy C, -C, -alkyl, C, -C, -alkylthio C, -C, -alkyl, C, -C, -po, J
alkoxyC r -C 5 or 6 and in each case containing 1 or 2 identical or different oxygen, nitrogen and sulfur atoms in the ring or substituted with 1 to 5 identical or different substituents; phenyl, phenyl C. -C,-alkyl, phenoxyC. -C. - represents alkyl, hetaryl or hetaryl C+Ca-alkyl or C8 and D together with the nitrogen atom to which they are attached may contain l or 2 double bonds l or 2 may contain individual identical or different oxygen, sulfur or nitrogen atoms and C ,-
form a 3- to 8-mononegative ring optionally substituted with 1 to 5 identical or different substituents from the group consisting of C ,-alkyl and CIC4-alkylcarbonyl, with the proviso that B is hydroxyl and,
When A has a meaning other than optionally substituted 7enyl or naphthyl, at least one group X,
Y or Z does not represent chlorine or methyl. A particularly preferred group of formula (r) is halogeno C in which B contains hydroxyl, methoxy, ethoxy, n- or in-propoxy, n-, iso- or tertiary-butoxy, fluorine and/or chlorine atoms. , -C4-alkoxy, or cycloalkoxy having 3 to 6 ring atoms, the cycloalkyl group being unsubstituted or containing l to 3 identical or Substituted by different substituents, X is hydrogen, fluorine, chlorine, methyl, ethyl, n- or isoprovir, methoxy, ethoxy, n- or i-proboxy, l, 2 or 3 fluorine and/or chlorine atoms halogenomethyl containing 1 to 5, in particular 1 to 3, fluorine and/or chlorine atoms, or in each case unsubstituted or 1 to 5 identical or represents phenoxy or phenylthio substituted by different substituents, the substituents selected for phenyl being fluorine, chlorine, bromine, methyl,
ethyl, n- or isobrovir, methoxy, ethoxy, n- or isobropoxy and trifluoromethyl, Y represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, and 2 represents fluorine or chlorine; n represents the number 0, l, 2 or 3, and A is methyl, ethyl, in each case linear or branched proyl, butyl, bentyl, hexyl, heptyl, octyl,
nonyl or decyl, nologenoC, -Ca-alkyl, C , -C . -alkenyl, C. -C. -alkynyl, C I- C 4-alkoxyC. -C4
-Alkyl or C: IC4-AlkylthioC. -C
．． - from 3 to 3 ring atoms which may represent alkyl or be interrupted by oxygen, nitrogen and/or sulfur;
6 cycloalkyl, or A is in each case unsubstituted or phenyl moiety of 1 to 5, especially 1 to
represents phenyl, benzyl or 7-enethyl substituted by three identical or different substituents, the substituents selected in each case being fluorine, chlorine, methyl, ethyl, n-
or isoprovir, methoxy, ethoxy, trifluoromethyl, tri7fluoromethoxy or in each case unsubstituted or 1 to 3 selected from the group consisting of fluorine, chlorine, methyl, methoxy, triple olomethyl and trinorolomethoxy selected from phenoxy or phenylthio substituted with the same or different substituents, with the proviso that if B represents hydroxyl and A has a meaning other than optionally substituted phenyl or naphthyl, at least One group X, Y or Z does not represent chlorine or methyl. A particularly preferred group of formula (1) is also those in which C/B represents the group N, in which \DC represents hydrogen, methyl, ethyl or n- or isobrovir, and D represents methyl, ethyl, n- or isobrovir. Itop mouth building, n
-, in-, secondary- or tertiary-butyl, allyl, probargyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, cyclopropyl, cyclobentyl, cyclohexyl, In each case unsubstituted or fluorine, chlorine,
represents phenyl, benzyl or phenethyl substituted by 1 to 5, in particular 1 to 3, identical or different substituents from the group consisting of methyl, ethyl and trifluoromethyl, or pyridyl or birimidyl; , or C and D together with the nitrogen atom to which they are attached may contain l or 2 double bonds or contain 1 further nitrogen, oxygen or sulfur atom. and methyl, ethyl,
forming a 5-1 or 6-membered ring optionally substituted with 1 to 3 identical or different substituents from the group consisting of methyl carbonyl and ethyl carbonyl, and X is hydrogen, fluorine, chlorine, methyl; , ethyl, n- or isobrovir, methoxy, ethoxy, n- or i
-proboxy, halogenomethyl containing 1, 2 or 3 fluorine B and/or chlorine atoms, halogenoethyl containing 1 to 5 fluorine and/or chlorine atoms, or in each case unsubstituted represents phenoxy or 7-enylthio substituted by 1 to 5 identical or different substituents, the substituents selected for phenyl being fluorine, chlorine, bromine, methyl, ethyl, n-
or inbrovir, methoxy, ethoxy, n- or isopropoxy and trifluoromethyl, Y represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, Z represents fluorine or chlorine, n represents the number OS 1, 2 or 3, and A is methyl, ethyl, in each case linear or branched proyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl, halogeno C, -C. -alkyl, Cj-C, -alkenyl, C. -C,-alkynyl, C,-C,-alkoxyC,-C,-alkyl or C. -C4-alkyl represents -C,-C,-alkyl or represents cycloalkyl with 3 to 6 ring atoms optionally interrupted by oxygen, nitrogen and/or sulfur; or It represents 7-enyl, benzyl or 7-enethyl, in each case unsubstituted or substituted by 1 to 5, in particular 1 to 3, identical or different substituents, the substituents selected in each case being fluorine, chlorine. , methyl, ethyl, n- or isoprovir, methoxy, ethoxy, tri7fluoromethyl, tri7
fluoromethoxy or 1 to 3 in each case unsubstituted or selected from the group consisting of fluorine, chlorine, methyl, methoxy, trifluoromethyl and trifluoromethoxy
7-enoxy or 7-enylthio substituted with identical or different substituents. A particularly preferred group of compounds is in which B represents hydroxyl, methoxy, ethoxy or n- or isopropoxy and X represents fluorine, chlorine or tri7fluoromethyl in the meta-position of the 7-enyl ring, or in each case represents 7-enyl or phenoxy, unsubstituted or substituted with 1 to 3 identical or different substituents, the selected substituents being fluorine,
chlorine, methyl and trifluoromethyl, Y represents hydrogen, fluorine or chlorine, n represents O and A is methyl, ethyl, n-globil, isoglobil,
n-, iso, secondary eleven or tertiary-
butyl, in each case straight-chain or branched pethyl,
Hexyl, hebutyl or octyl, halogen-Cr
Cs-alkyl, allyl, probargyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cycloprobyl, cyclopentyl, cyclohexyl, or in each case unsubstituted or fluorine, chlorine, tri7fluoromethyl, 7enoxy and 4-tri 7enino substituted with 1 to 3 identical or different substituents from the group consisting of 7fluoromethyl-7enoxy; It represents benzyl or benzyl. A particularly preferred group of formula (I) is also those in which C/B represents the radical N, where \DC represents hydrogen and D is methyl, ethyl, n- or isogropyl, n
represents 7-enyl substituted by 1 to 3 identical or different substituents from the group consisting of fluorine, chlorine and tri7fluoromethyl, or C and D together with the nitrogen atom to which they are attached may be optionally substituted by 1 to 3 identical or different substituents from the group consisting of methyl, ethyl, methylcarbonyl and ethylcarbonyl; : represents a heterocyclic group in which 7-enyl or phenoxy, the substituents selected are fluorine, chlorine, methyl and trifluoromethyl, Y represents hydrogen, fluorine or chlorine, n represents O and A represents methyl, ethyl, n -probyl, isoprovinole, n-, iso, secondary or tertiary-butyl, in each case straight-chain or branched bentyl, hexyl, hebutyl or octyl, halogen-C
．． -C,-alkyl, allyl, propargyl, methoxymethyl, methoxyethyl, ethoxymethyl, dithoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, or in each case unsubstituted or fluorine, chlorine, trifluoromethyl, phenoxy and 4-tri represents phenyl or benzyl substituted with 1 to 3 identical or different substituents from the group consisting of fluoromethyl-phenoxy. In all the above definitions, special mention should be made of the meaning of X being trifluoromethyl in the meta position of the phenyl ring. N-(3-1-ri7fluoromethyl7enylacetyl)-
General method for producing ethyl N-methyl-aminoacetate (a)
When used according to the present invention, the steps of the process according to the invention can be represented by the following reaction scheme: If methyl p-toluenesulfonate is used as starting material according to general preparation method (a), the steps of the process according to the invention can be represented by the following reaction scheme: 3-(3-}lifluoromethyl If 7enyl)-1-isoprobyl-pyrrolidine-2,4-dione and methylamine are used as starting materials according to general process (c), the steps of the process according to the invention are represented by the following reaction scheme: Can: CH. -NH-A in which R1 represents hydrogen or alkyl, in particular methyl or ethyl, and A has the meaning given above, are prepared in a general manner (Chemical Reviews, CheIII. Rev.), 5
2 (1953), 237-4 16 and Organicu+a, 9th edition, 446
(1 970) VEB Deutschenolle 7 Enollerag (see Denore Wissenschaften), formula (VI) are known or can be easily prepared by methods known in principle. Thus, for example, N-acylamino acid esters of formula CTi) are of formula (V)

[In the formula, Hal represents halogen, in particular fluorine, chlorine or bromine, and x, y, z and n have the above meanings by an acylation method using 7-enyl acetyl halides of 1,
Alternatively, N-acylamino acids of formula (II) in which Rl represents hydrogen can be prepared by a conventional method (Chem.Ind., London).
1568 (1968)). A compound of formula (If) in which R' represents hydrogen is, for example, a compound of formula (V
It can also be obtained from 7-enylacetyl halides and amino acids of I). Compounds of formula (V) are obtained from α-halogenocarboxylic acids or esters and amines by methods known from the literature (Advanced Organic Chemistry).
try), J. March, 3 7 7 pages, Matsuku Grow Hill Incorporated, (19
77)). Phenylacetyl halides of formula (Vl) are known organic chemical compounds. Examples include compounds of formula (II) below.1. N
-(3-trifluoromethylphenylacetyl)-N-
Isopropylaminoethyl acetate2. N- (3-trifluoromethylphenylacetyl')-N- (1,1.
3.3-tetramethyl)butylaminoethyl acetate3. N-(3-1 Lifluoromethylphenylacetyl)-N-2.4.6- Ethyl trimethylphenylaminoacetate4. Ethyl N- (3- 7-fluoromethylphenylacetyl)-N-cycloptylaminoacetate5. N- (
3-to! J fluoromethylphenylacetyl)-ethyl N-cyclobentylaminoacetate6. N- (3-t'
) Fluoromethyl7enylacetyl) Ethyl-N-cyclohexylaminoacetate7. N-(3-1-trifluoromethyl7enylacetyl)-N-(2-methoxyshetylaminoethyl acetate8.N-(3-trifluoromethylphenylacetyl')1N-(1-tri7enylacetyl) methylethyl)butylaminoacetate 9.N- (3-}lifluoromethylphenylacetyl)-1N-phenylaminoethyl acetate 10.N-(3-trifluoromethylphenylacetyl)-N-2-chlorophenylaminoethyl acetate 1 1.N- (3-}Refluoromethylphenylacetyl)-N-4-chlorophenylaminoethyl acetate 12.N- (3-tri7fluoromethyl7enylacetyl)-N-2.4-dichlorophenylaminoacetic acid Ethyl 13.N-(3-trifluoromethylphenylacetyl)-N-2.6-dichloro-7enylaminoethyl acetate 14.N-(3-1-trifluoromethylphenylacetyl)-N-4-tri7 ethyl fluoromethyl7enylaminoacetate 15.N- (3-tri7fluoromethylphenylacetyl)-N-2-fluoromethylphenylaminoethyl acetate 16.N- (3-1-trifluoromethylphenylacetyl)-N- 5-Trifluoromethyl7enylaminoethyl acetate 17.N- (3-t!J7fluoromethylphenylacetyl)-N-2-7fluoro7enylaminoethyl acetate 18.N- (3-trifluoromethylphenylacetyl) acetyl)-N-4-fluorophenylaminoacetate ethyl 19.N-(3-trifluoromethylphenylacetyl)-N-2.6-difluorophenylaminoethyl acetate 20.N-(3-tri7 21.N-(3-trifluoromethylphenylacetyl)-N-2.4-difluoromethylphenylaminoacetyl ethyl acetate 22.N-( 3-Trifluoromethylphenylacetyl)-N- 1.2.2- }Limethylbutylaminoethyl acetate23.N- (3-trifluoromethylphenylacetyl)-N-pendylyaminoethyl acetate24.N-7enylacetyl N-(3-}realolomethylphenyl)aminoethyl acetate 25.N-7 enylacetyl N-
Ethyl cyclopropylaminoacetate26. Ethyl N-(3-trifluoromethyl7enylacetyl)-N-1.2-dimethylpropylaminoacetate27. Ethyl N-(3-trifluoromethylphenylacetyl)-N-3.4-dichlorophenylaminoacetate28. Ethyl N-(2,4.6-trichloro-3-7luor-5-phenoxy7enylacetyl)-N-7henylaminoacetate29. N-(4-}-7fluoromethyl-2-chloro6-7fluoro7enylacetyl) -N-7enylaminoethyl acetate 30. Ethyl N-(3-tripleomethylphenylacetyl)-N-3-chlorophenylaminoacetate31. N-7enyl acetyl-N-7enylmethylaminoethyl acetate32. N-phenylacetyl-N-2.4-di7fluoro7enylaminoethyl acetate33. N- (2-(2,4-dimethyl-7-enoxy)7
34. Ethyl N- (2-7 enoxyphenylacetyl)-N-7 phenylaminoacetate 35. Ethyl N-(3-trifluoromethylphenylacetyl)-N-4-7enoxy7enyl)aminoacetate36. Ethyl N-(3-trifluoromethylphenylacetyl)-N-4-(4-trifluoromethylphenoxy)phenylaminoacetate37. N- (4-tri7
Ethyl (fluoromethyl-2-chloro-6-fluorophenylacetyl)-N-phenylaminoacetate38. N-7enylacetyl-N-2-chlorophenyl-aminoethyl acetate39. N- (2,4-difluoro7enylacetyl)
-N-3-tri7fluoromethylphenylaminoethyl acetate 40. N-(3-trifluoromethylphenylacetyl)-N-(3-tri7-methyl-7enyl-4-7
enoxy7enyl) monoaminoethyl acetate41. N-yenylacetyl-N-3-chloro7enylaminoethyl acetate42. N-7enylacetyl-N-4-chloro7enylaminoethyl acetate43. N-phenylacetyl-N-3.4-dichlorophenylaminoethyl acetate 44. Ethyl N-(3-trifluoromethylphenylacetyl)-N-methylaminoacetate45. N- (3-
46. Ethyl trifluoromethylphenylacetyl-N-tert-butylaminoacetate 46. N-(3-7 enoxyphenylacetyl)-N
-Phenylaminoethyl acetate47. N- (3-phenoxyphenylacetyl)-
Ethyl N-(3-tri7fluoromethyl7enyl)monaminoacetate48. Ethyl N-(4-phenoxyphenylacetyl)-N-7enylaminoacetate49. N- (phenoxy7enylacetyl)-N-
(tri7fluoromethylphenyl)monoaminoethyl acetate50. N-(3-tri7fluoromethyl7enylacetyl)-N-(4-cyclohexyl7enyl)-ethyl aminoacetate51. N-(2-phenoxy7enylacetyl)-N
- (3-trifluoromethylphenyl)monoaminoethyl acetate52. N-7enylacetyl-N-(4-fluoro7enyl)monaminoethyl acetate53. Ethyl N-(3-trifluoromethylphenylacetyl)-N-(2-methylphenyl)monaminoacetate54. N-(3-trifuracetyl-7enylacetyl)-N-(3-methylphenyl)monoaminoacetic acid
Chill 55. Ethyl N-(3-trifluoromethylphenylacetyl)-N-(4-methylphenyl)monaminoacetate56. N-(4-methyl7enylacetyl)-N-(
4-7 fluorophenyl) monoaminoacetic acid ethynole57. N- (2-methyl7enylacetyl)-N-
(4-fluoro7enyl)monoaminoacetic acid ethynole58. N- (2-methylphenylacetyl)-N-
(3-7fluorophenyl)monoaminoacetic acid ethynole59. N- (2-fluorophenyl acetyl)-N-
(2-methylphenyl)monoaminoacetic acid ethynole60. N- (4-7fluoro7enylacetyl)-N-
(2-methylphenyl)monoaminoethyl acetate61. N-(2-fluorophenylacetyl)-N-
(4-methylphenyl)monoaminoethyl acetate62. N- (2-7fluoro7enylacetyl)-N-
(3-methylphenyl)monoaminoethyl acetate63. N- (4-fluoro7enylacetyl)-N-
7Phenylaminoethyl acetate64. N- (4-fluorophenylacetyl)-N-
(3-chlorophenyl)monoaminoethyl acetate65. N-(2,4-di7fluoromethylphenylacetyl)-N-(4-fluorophenyl)-aminoethyl acetate66. N-(2,4-di7fluoromethylphenylacetyl)-N-(2-methylphenyl)monoaminoethyl acetate67. N-(2,4-di7-methyl-7enylacetyl)-N-(3-methylphenyl)monaminoethyl acetate68. Ethyl N-(2,4-di7fluoromethylphenylacetyl)-N-(4-methyl7enyl)monaminoacetate69. N-(2,4-di7fluoromethyl7enylacetyl)-N-(2,4-di7fluoromethyl)monoaminoethyl acetate70. N-(3-7fluorophenylacetyl)-N-
(3-Methyl7enyl)monoaminoethyl acetate71. ．． N-(3-fluoro7enylacetyl)-N-
(4-methylphenyl)monoaminoethyl acetate72. N- (3-fluorophenylacetyl)-N-
(3-fluorophenyl)monoaminoethyl acetate73. Ethyl N-(2-methyl7enylacetyl)-N-phenylaminoacetate. The B-hydroxyl of formula (I) required as starting material for carrying out the processes (b) and (c) according to the invention
) is a compound according to the invention and the method (
Obtained by a). The alkylating reagents of formula 1) additionally required as starting materials for carrying out process (b) according to the invention are known organic chemical compounds. In formula (IIF), R2 is preferably CI CIO
-alkyl, halogeno CI-CIO-alkyl or cycloalkyl having 3 to 7 ring atoms, the cycloalkyl group being unsubstituted or fluorine, chlorine, bromine and C. substituted with 1-5 identical or different substituents from the group consisting of -C,-alkyl; R2
particularly preferably stands for methyl, ethyl, probyl or isobyl. In formula (n[), %X' is preferably chlorine, bromine or the element C. -C,-alkylsulfonyloxy, C.
-C. -alkoxysulfonyloxy or p-toluenesulfonyloxy, such as methanesulfonyloxy,
Represents methoxysulfonyloxy or ethoxysulfonyloxy. The alkylating reagent of formula (II[) is a known organic chemical compound. The amines of the formula (IV) necessary as starting materials for carrying out the process (c) according to the invention are generally known compounds or can be prepared by known methods (Houben-Weyer). -Weyl), Mesoden
Der organischen hemi (Methoden)
der Organischen Chemie),
XI/Volume I, George Cheme●Ferlag, Stuttgart,! 957). Process (a) is characterized by subjecting the compound of formula (II) to an intramolecular condensation in the presence of a base. Diluents that can be used in process (a) according to the invention are all common inert organic solvents. Solvents that can be suitably used are hydrocarbons, such as toluene and xylene, and ethers, such as diptyle ether, tetrahydro-7
ran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and polar solvents such as dimethynoresnorefoxide, snorephoran, dimethynorephonolemamide and N-methyl-pyrrolidone. Deprotonating agents that can be used in carrying out process (a) according to the invention are all common proton acceptors. Proton acceptors that can be preferably used are alkali metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate; They can also be used in the presence of phase transfer catalysts, such as triethylbenzylammonium chloride, tetrabutylammonium bromide, Adgen 464 or TDA I. Alkali metal amides and hydrides and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and alkali metal alcoholates,
For example, sodium methylate and potassium tertiary butyrate can also be used. Adgen 464 Methyltrialkyl monochloride (Cs C
+. ) ammonium TDA 1-}lisu(methoxyethoxyethyl)
monoamine The reaction temperature when carrying out process (a) according to the invention can vary within a substantial range. Generally the reaction is Q
between 00°C and 250°C, preferably between 50°C and 150°C
It is carried out at a temperature between . Process (a) according to the invention is generally carried out under normal pressure. To carry out process (a) according to the invention, formula (II) and the reaction or class of deprotonating bases are generally used in approximately equimolar amounts. However, it is also possible to use relatively large excesses (up to 3 moles) of either of the precept classes. The reaction is generally carried out in a suitable diluent. Diluents that can be used in process (b) according to the invention are inert organic solvents. Solvents which can be preferably used are aliphatic, cycloaliphatic or aromatic, optionally halogenated hydrocarbons, such as benzine, benzene, tonoleene, xylene, benzene, hexane, heptane, cyclohexane, petroleum ether. , ligroin, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene or dichlorobenzene, monoethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydro7rane or ethylene glycol diethyl or dimethyl ether, ketones such as acetone, butanone , methinolysoglobinoleketone or methinolysobutylketone, esters such as methyl acetate, acids such as acetic acid, nitriles such as acetonitrile or probionitrile, and amides such as dimethylformamide, dimethylacetamide, N-methinore pyrrolidone or hexamethylphosphoric triamide. When using a liquid compound of formula Cm) as a reaction partner,
They can also be used as diluents at the same time in a corresponding excess. Acid-binding agents that can be used in process (b) according to the invention are all commonly used inorganic and organic bases. Preferred bases used are alkali metal hydrides, hydroxides, amides, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium hydroxide, sodium carbonate or sodium hydrogen carbonate, or tertiary amines, such as triethylamine,
N,N-dimethylaniline, pyridine, 4-(N,
N-dimethylamino)-pyridine, diazabicyclooctane (DABCO), diazabicyclononene (D B
N) or diazabicycloundecene (DBU). The reaction temperature when carrying out process (b) according to the invention can vary within a substantial range. Generally the reaction is -2
Between 0°C and +150' (:!, preferably 50
It is carried out between °C and +100 °C. To carry out the process (b) according to the invention, in general, in each case from 1 to 20 mol, preferably in each case 1 -1 mol, per mol of a compound of the formula (I) in which B represents hydroxyl.
5 mol of an alkylating agent of formula (I[I) and optionally 1-
3 mol, preferably 1 to 2 mol, of acid-binding agent are used. The reaction is carried out and the reaction product of formula (I) is worked up and isolated by conventional methods (see also Preparation Examples). Suitable usable diluents for carrying out process (C) according to the invention are inert organic solvents. These include, in particular, aliphatic, cycloaliphatic or aromatic, optionally halogenated hydrocarbons, such as benzine, ligroin, benzene, toluene, xylene, chlorobenzene, petroleum ether, bentane, hexane, hebutane. , cyclohebutane, methylene chloride, chloroform and carbon tetrachloride, ethers such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol diethyl or dimethyl ether, ketones such as acetone or putanone, nitriles such as acetonitrile or probionitrile, Amides, such as dimethylformamide, dimethylacetamide, N
-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide, or esters such as ethyl acetate. It is also possible to use liquid amines of the formula (rV) as solvents in a corresponding excess. Optionally, process (c) according to the invention is carried out in the presence of a dehydrating agent. Dehydrating agents preferably used are alkali metal carbonates, such as potassium carbonate, molecular sieves or catalytic amounts of, for example p-toluenesulfonic acid. Azeotropic removal of water by distillation during the reaction is a preferred step. The reaction temperature when carrying out process (c) according to the invention can vary within a substantial range. Generally the reaction is carried out at O℃
The method (c) according to the invention is generally carried out under normal pressure. It is also possible to carry out the process (c) according to the invention using l-10 mol, preferably about 1 mol per mol of a compound of formula (I) in which B represents hydroxyl. ~2.5 mol of formula (IV
) of amine and optionally 1 to 5 mol of dehydrating agent are used. The reaction is carried out and the reaction product of formula (I) is worked up and isolated by conventional methods. The active compounds according to the invention can be used as defoliants, desiccants, hardwood destroyers and, in particular, as weedicides. Weeds, in the broadest sense, mean any plant that grows in a place where it is not desired. The substances according to the invention act essentially as complete or selective herbicides depending on the amount used. The compounds according to the invention can be used, for example, in connection with the following plants: Dicotyledonous weeds of the following genera: S inapis,
L epidium, Galium, S tell
aria), Matricaria, A r+thamis, G al insoga, Chophyllaceae (C h
enopodium), Urtica,
Genus Chion (S enec iO), Genus Hu (A m
a. ranthus), Portulaca spp.
ulaca), X anthiuz, Convolvulus, I pomoea, Polygonum
), Sesbania, Ambrosia, Cirsium
ium), Cardus, Sonchus, Solan
um), Rorippa, Rotala, L indernia
), Lamium, V sronica, Abutil
on), Emex, Datura (1) atura, Viola, Ga leopsis, Papas and Centaurea ((:
Htaurea). Dicotyledonous cultivated plants of the following genera: Gossypi
um), Glycine, Beta, Daucus, Phaseolus, Pea (
Pisum), Solanum, Linum, Ipomoea
), Vicia, Nicotiana
tiana), Tomato genus (Lycopers icon)
), Arachis, Brassica (
Brassjca), Lactobacillus (Lac
tuca), Cucumis and Cucurbita. Monocotyledonous weeds of the following genera: E chinochlo
a), S etaria, Millet (
P anicum)s D igita
ria), Phleum, Poa, Festuca
), E leusine, Brachiaria, Loli
um), Bromus, Avana, Cyperus (C y
perus), sorghum (S orghuo+),
A gropyron, Cynodon, Monochar
ia), F imbristylis,
Genus Omodaka (S agittaria), Genus Harii (
E leocharis), S cirp
us), Paspalum, T schaemum, Sphenoclea, Dactyloctenium, Nucabo (
A grostis), A grostis (A lo
pecurus) and Apera. Monocotyledonous cultivated plants of the following genera: Oryza, Zea, Triticum
m), barley (H ordeum), oat (A vena), rye (Secale)
), Sorghum, Millet (P
anicum), Saccha
rum), A nanas, A sparagus and A fi (A
llium). However, the use of the active compounds according to the invention is in no way restricted to these genera, but extends in the same way to other plants. Depending on the concentration, the compounds are suitable, for example, for the complete control of weeds in industrial areas and on railway lines, on roads and squares with or without trees. Equally, the compounds can be used in perennially cultivated plants, such as silviculture, ornamental trees, orchards, vineyards, citrus groves, walnut orchards,
For control of weeds in banana plantations, coffee plantations, tea plantations, rubber tree plantations, oil palm plantations, cocoa plantations, small fruit tree plantings and hop cultivation plants, and in annual cultivation plants. It can be used for selective control of weeds. The active compounds of formula (I) according to the invention are particularly suitable for selectively controlling dicotyledonous weeds in monocotyledonous and dicotyledonous crops by pre- and post-emergence methods. The compounds according to the invention furthermore exhibit activity as foliar insecticides. The active compounds can be present in the customary formulations, for example solutions, emulsions, wettable powders, suspensions, powders, dusts, liniments, soluble powders, granules,
Suspensions can be converted into very fine capsules in emulsion concentrates, natural and synthetic substances impregnated with the active compound, as well as polymeric substances. These formulations are prepared in known manner, for example, by mixing the active compound with extenders, i.e. liquid solvents and/or solid carriers, and optionally surfactants, i.e. emulsifiers and/or dispersants and/or blowing agents. Ru. Furthermore, when water is used as an extender, for example, an organic solvent can also be used as an auxiliary solvent. As a liquid solvent,
Mainly aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, for example cyclohexane, or paraffins such as mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, For example, dimethylformamide and dimethylsulfoxide and water are suitable. As solid carriers, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals such as highly dispersed silicic acids, aluminas and silicates are suitable. Suitable as solid carriers for granules are ground and fractionated natural rocks, such as calcite, marble, pumice, sepiolite and dolomite, as well as inorganic and organic mixtures or granules and granules of organic substances, such as sawdust, Palm, corncobs and tobacco stalks are suitable; as emulsifiers and/or blowing agents non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers 4RL, alkylarylboly Suitable are glycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates and albumin hydrolysis products; suitable cleavage agents are, for example, lignin sulfite waste liquor and methylcellulose. Adhesives such as carboxymethylcellulose and powdered, granular or latex natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as ceramine and lecithin, and synthetic phospholipids, are applied to the skin. Can be used. Further additives can be mineral and vegetable oils. Colorants, such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes and metallurgical talocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybten and zinc. can be used. The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%. For controlling weeds, the active compounds according to the invention can also be used as such or in the form of their preparations as mixtures with known herbicides, finished preparations or bath mixing being possible. . Classes that can be used for mixtures include known herbicides, such as aryloxyallic acids, such as 2.4D, 2.4D
P, 2.4-DB, MCPA, MCPP, 7 fluoroxyvir, aryloxyphenylalkanoic acid esters, such as diclof, 7 enoxaprop, 7 noreadibutyl, quizalofop, and haloxyfop, arylcarboxylic acids, such as Clopyralid, azinones such as chloridazone and norfurazone, carbamates such as 7emedipham, furo7am, chloropro7am and aslam, chloroacetanilides such as alachlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor, dinitroanilines such as oryzalin , pendimethalin oyohytrifluralin, diphenyl ethers such as acifluorfen, bifenox, fomesa-7ene, lactofen and oxy-7olfen, ureas such as chlortoluron, fluorometuron, isoproturon and metabenzthiazuron,
hydroxylamines such as alloxydim, cycloxydim and sethoxydim, imidazolinones such as imazetavir, imazametabenz and imazaquin,
Nitriles, such as promoxynil and ioxynil, oxyacetamides, such as me7enacet, sulfonylure7, fi, tlf pensulon, chlorimuron, chlorsulfuron, methasulfuron and thiameturon, thiolylbamates, such as cycloate, EPTC, molinate, thiobencarb and trialalt, triazinediones such as amethidione, triazines such as atrazine, cyanazine, simazine, simethylline and terbutulin, or triazines such as ethiozine, hexazinone, metamitrone or metribuzine, or other bentazones such as synmethyline. , funorelidone, sateviridate, and dimethasone. Surprisingly, certain mixtures also exhibit synergistic activity. Furthermore, other known active compounds, such as fungicides (f.
ungicides), insecticides (insecti)
acaricides), acaricides,
Nematicides, small bird repellents,
Mixtures with plant nutrients and soil amendments are possible. the active compounds as such or in the form of their preparations or further diluted forms of use;
For example, ready-to-use solutions,
They can be used in the form of suspensions, emulsions, powders, coatings and granules. These can be carried out by conventional methods, such as watering, spraying, etc.
ing), atomizing or scattering. The active compounds according to the invention can be applied before or after germination of the plants. They can also be added to the soil before sowing. The amount of active compound used can vary within a substantial range. This essentially depends on the nature of the desired effect. In general, the usage rate is 0.00 per hectare of soil surface.
Between 1 and 1 kg, preferably between 0.01 and 5 kg. The preparation and use of the active compounds according to the invention can be seen from the examples below. Process (a) 3-(3-}lifluoromethylphenyl)-1-isoprobyl-pyrrolidine-2,4-dione
-1-Lifluoromethyl-phenylacetyl)-N-ingropyruaminoacetate was dissolved in 3.6 g (0.12 mol) of 80% strength sodium hydride in 55 mff of anhydrous toluene at 95-100°C. It was added in full over about 60 minutes. The mixture was then subsequently stirred at 100° C. for a further 1 hour and, while cooling using a water bath, 30 mQ of ethanol, then 80 rtrQ of water and then 10 mQ of concentrated hydrochloric acid were added dropwise. was filtered off with suction, thoroughly rinsed first with water and then with petroleum nitrate and dried.Colorless crystals of raw material were obtained.5.
1.1 g (78.2% of theory), melting point 207-
208℃. Process (a) in a manner analogous to Example I and according to the invention
Taking into account the instructions given in Table 1 below, the final products of formula (I), in which B represents hydroxyl, are obtained. 8 3 - CF 3 H 15 3-CF, H / -CH \ CF, CH, 3 184 16 3-CF3 17 3-CF, 18 3-CF. l9 3-CF. 20 3-CF. 2l 3-CF. 22 3-CF. 23 3-CF3 24 H 25 H 26 3 -CF. 27 3-CF. Cl 30 3 -CF, 31 H 32 H H H H H H H H H H H H H CF3 F C H 2 C (CH 3 ) 3CH (CH
s) (CH3)3 CH(CH3) CH(CH3)! (71 242 125 193 CH3 35 3 -CF3 36 3 -CF3 r1 39 2-F 40 3-CF, 4l H 42 H 43 H 44 3-CF. 45 3-CF, H H 4-F H H H H H H CH, C(CH3)3 260 〉230 57 2-CH. H 58 2-CH, H 65 2.4-Fz H CH3, 2.4-F* H'; l-Me H Example 41a Method (c) Stirring with 3-(3-1-di7fluoromethyl7enyl)-1-isobrobyl-4-(N-methylamino)-3-pyrroline-2-dione, filtering off with suction and drying. 6.7 g (91% of theory) of product (colorless crystals) were obtained, melting point 161-2° C. In a manner similar to Example 41 and according to the method according to the invention (C
), the formula (I
) was obtained. 62.4g of 32% strength aqueous methylamine solution was added to 5Qm
8.5 g (0.1 mol) of 3-(3-}refluoromethylphenyl)-1-isopropyl-pyrrolidine-2,4-dione ( prepared according to Example 1). The mixture was heated using a water separator for 4 hours. It was then concentrated in vacuo and the remaining crude raw material was added to 300 mQ of water and the mixture was
Extracted twice with ml2 methylene chloride and the combined extracts were concentrated in vacuo. Example 156 Method (b) 3-(3-t!Jfluoromethyl7enyl)-1-1-Shari-butyl-4-methoxy-3-viroline-2 −
3.89 g (13 mmol) of 3-(3-
} tert-methylphenyl)-1-tert-butyrolidine-2,4-dione is suspended in 30 mQ of anhydrous acetonitrile, and then 0.0 mQ dissolved in 5+*Q of anhydrous acetonitrile is suspended. 8 4 g (15 mmol) of powdered potassium hydroxide and 2.8 g (15 mmol) of powdered potassium hydroxide
After the addition of methyl p-tonolenesnolephonate, the mixture was refluxed for 3 hours. That 2001I
14 of water with stirring, extracted with methylene chloride, and the extracts were dried and concentrated. The residue was purified by column chromatography on silica gel using cyclohexane/ethyl acetate 1:2. After crystallization from ether/n-hexane, 2.03 g
(47.2% of theory) has a melting point of 129°C.
-trifluoromethylphenyl)-1-butyl-4-methoxy-3-virolin-2-one was obtained. Similarly, the following compounds were obtained. Example 157 3-(3-trifluoromethylphenyl)-1
-(2-methoxyethyl)-4-methoxy-3-pyrrolin-2-one, 56.2% yield, oil. USE EXAMPLES Example A Post-emergence Test Solvent: 5 parts by weight of acetone emulsifier = 1 part by weight of alkylaryl polyglycol ether To prepare a suitable formulation, 1 part by weight of active compound was added to the above amount of active compound. The solvent was mixed, the above amount of emulsifier was added, and the mixture was diluted with water to the desired concentration. 5 Test plants 15 cm high were sprayed with the active compound formulation in such a way that the desired specific amount of active compound per unit area was applied. The concentration of the spray liquid was chosen such that the desired specific amount of active compound of 2.000 liters of water/ha was applied. After 3 weeks, the degree of plant damage was evaluated in % damage compared to untreated control growth. The values indicate: 0% = no activity (as for untreated control) lOO% = complete kill. In this test compounds 81, 89 and 92 showed very good herbicide activity against dicotyledonous weeds and
It showed very good tolerance to crop plants such as in wheat or barley. Example B Pre-emergence Test Solvent: 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable formulation of active compound, 1 part by weight of active compound is mixed with the above amount of solvent. The above amount of emulsifier was added, and the mixture was diluted with water to the desired concentration. The seeds of the test plants were sown in normal soil and after 24 hours were sprayed with the active compound formulation. It is convenient to keep the amount of water per unit area constant. The concentration of active compound in the formulation is not important, only the amount of active compound per unit area. After 3 weeks, the degree of plant damage was determined by % compared to untreated control growth.
Evaluated based on damage rate. Values indicate 0% - no activity (as for untreated control) 100% = complete kill. In this test, compounds 81, 88, 89 and 92 showed very good herbicide activity against monocotyledonous and dicotyledonous weeds and good tolerance against crop plants such as in barley, corn, soybean or cotton. . The main features and aspects of the invention are as follows. 1. General formula (I) [wherein X and Y independently of each other represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, or in each case unsubstituted or substituted aryloxy or arylthio, Z is halogen, represents alkyl or alkoxy, n represents the number 0, 1, 2 or 3; A is in each case unsubstituted or in each case halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl; , cycloalkyl optionally interrupted by heteroatoms, unsubstituted or halogen,
represents arylalkyl substituted by alkyl, halogenoalkyl, alkoxy and/or nitro, or unsubstituted or substituted aryl, in which the possible substituents are halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or in each case Both are phenoxy or phenylthio, which is unsubstituted or substituted by halogen, alkyl, alkoxy, halogenoalkyl and/or halogenoalkoxy, and B represents hydroxyl, alkoxy, halogenoalkoxy or cycloalkoxy, and the cycloalkyl group is unsubstituted. or substituted by halogen and/or alkyl, or B represents a group N in which C8 and D independently of each other are hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl , cycloalkyl, optionally interrupted by a heteroatom, or in each case unsubstituted or substituted 7enyl, 7enylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl, or C and D are together with the nitrogen atom to which they are attached, form an optionally substituted ring which may be optionally interrupted by 3 to 9 member heteroatoms, provided that 4-, where B represents hydroxyl and A has a meaning other than optionally substituted aryl, at least one group X, Y or 2 does not represent chlorine or methyl] Alkoxy and 4-(II-substituted)amino-3-arylvirolinone derivatives. 2. X and Y are independently hydrogen, fluorine, chlorine,
Bromine, iodine, CI-C. -alkyl, ClCs-alkoxy, halogenoC+Ca-alkyl or 7enoxy or 7enylthio in each case unsubstituted or substituted by 1 to 5 identical or different substituents, the substituents selected for 7enyl; is fluorine, chlorine,
Bromine, iodine, C,-C,-alkyl, C. -C. -Alkoxy and halogen-C. - C,-alkyl, Z represents fluorine, chlorine, bromine, iodine, CrCa-alkyl or C,-C,-alkoxy, n represents the number 0, 1, 2 or 3, and A is in each case Unsubstituted or in each case halogen-substituted CI-CI! -alkyl, C,C,-alkenyl, C,-C,-alkynyl, CI-C1. -alkoxy C, -C, -alkyl, C1C. -Borialkoxy10 r-C a-alkyl? is C. -C.
．． -Alkylthio 10, -C, -alkyl,
or represents cycloalkyl with 3 to 8 ring atoms optionally interrupted by oxygen, nitrogen and/or sulfur, or A is in each case an unsubstituted or 7-enyl moiety with 1 to 5 identical or represents phenyl 10,10,-alkyl, 7-enyl or naphthyl substituted by different substituents, the substituents selected in each case being fluorine, chlorine, bromine, iodine, CI-C. -alkyl, C. −
C,-alkoxy, halogenoC. -C. one alkyl,
Halogeno C, -C, -alkoxy; is in each case unsubstituted or fluorine, chlorine, bromine, iodine, C, -C
, -alkyl, C , + C , + alkoxy, halogeno C, -C, -alkyl and halogeno C, -C,
-alkoxy, phenoxy or phenylthio substituted with 1 to 5m identical or different substituents selected from the group consisting of B is hydroxyl, C, -C, . -alkoxy, halogeno C, -C■. -alkoxy or ring atoms from 3 to 7
cycloalkoxy, the cycloalkyl group being unsubstituted or containing fluorine, chlorine, bromine and C, -C,
- substituted by l to 5 identical or different substituents from the group consisting of alkyl, or C/B represents a group N, in which \D C and D independently of each other are hydrogen, C, -C,
．． -alkyl, c3CIO-alkenyl, C,+-
C. -Alkoxy C. -C,-alkyl, C. −
C,-alkylthioC,-C,-alkyl,C,-C
,-Polyalkoxy C t ”- C s-alkyl, L1 3 to 3 ring atoms optionally interrupted by 2 or 3 identical or different oxygen, nitrogen and sulfur
8 cycloalkyl, or t; has 5 ring atoms in each case
or 6 and more preferably l or 2 identical or different oxygen, nitrogen and sulfur atoms in the ring, in each case unsubstituted or substituted with 1 to 5 identical or different substituents Phenyl, phenyl-C, -
C. -alkyl, phenoxy10+Ca-alkyl, hetaryl or hetaryl C, -C. - represents alkyl or C and D together with the nitrogen atom to which they are attached may contain l or 2 double bonds or l or 2 further identical or different It may contain oxygen, sulfur or nitrogen atoms, and C + −
forms a 3- to 8-membered ring optionally substituted with 1 to 5 identical or different substituents from the group consisting of CI-alkyl and CI04-alkylcarbonyl, with the proviso that B is hydroxyl; and when A has a meaning other than optionally substituted phenyl or naphthyl, at least one group X,
4-alkoxy and 4-(substituted)amino-3-arylvirolinone derivatives of formula (1) of 1 above, wherein Y or Z does not represent chlorine or methyl. 3. B is hydroxyl, methoxy, ethoxy, n- or isoproboxy, n+, iso secondary-
or halogeno C.I containing tertiary poxy, fluorine and/or chlorine atoms. -C,-alkoxy or cycloalkoxy having 3 to 6 ring atoms, the cycloalkyl group being unsubstituted or 1 to 3 from the group consisting of fluorine, chlorine, methyl and ethyl;
is substituted with the same or different substituents,
X is hydrogen, fluorine, chlorine, methyl, ethyl, n- or isobrovir, methoxy, ethoxy, n- or i
-proboxy, halogenomethyl containing 1, 2 or 3 fluorine and/or chlorine atoms, halogenoethyl containing 1 to 5, especially 1 to 3 fluorine and/or chlorine atoms; , or 7enoxy or 7enylthio, in each case unsubstituted or substituted with 1 to 5 identical or different substituents,
Substituents selected for phenyl are fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl, methoxy, ethoxy, n- or isopropoxy and trifluoromethyl, and Y is hydrogen, fluorine, chlorine, methyl, represents ethyl, methoxy, ethoxy or tri7fluoromethyl, Z represents fluorine or chlorine, n represents the number 0, L represents 3, and A represents methyl, ethyl, in each case a straight or branched chain. Propyl, butyl, pentyl, hexyl, hebutyl, octyl, nonyl or decyl, halogeno C. -C. -alkyl, CsC*-alkenyl, C, -C. -alkynyl, C, -C, -alkoxyC. -C,-alkyl or C,-C4-alkylthio-C,-C4-alkyl or cycloalkyl with 3 to 6 ring atoms optionally interrupted by oxygen, nitrogen and/or sulfur , or A represents 7-enyl, benzyl or 7-enethyl, in each case unsubstituted or substituted in the phenyl moiety by 1 to 5, in particular 1 to 3, identical or different substituents, selected in each case Substituents include fluorine, chlorine, methyl, ethyl, n- or isobrovir, methoxy, ethoxy, trifluoromethyl,
trifluoromethoxy or in each case unsubstituted or 7-enoxy or substituted by 1 to 3 identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, methoxy, trifluoromethyl and trifluoromethoxy; 7enylthio, with the proviso that if B represents hydroxyl and A has a meaning other than optionally substituted phenyl or naphthyl, then at least one group 4-alkoxy and 4-(substituted)amino-3-arylvirolinone derivatives of formula (1) of l above, which do not represent chlorine or methyl. 4. C represents hydrogen, methyl, ethyl or isoprovir, and D represents methyl, ethyl, n- or isoprovir, n
-, iso, secondary or tertiary butyl, allyl, globargyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, cyclopentyl, cyclopentyl, cyclohexyl, in each case unsubstituted or fluorine, chlorine,
represents 7-enyl, benzyl or 7-enethyl substituted by 1 to 5, in particular 1 to 3, identical or different substituents from the group consisting of methyl, ethyl and trifluoromethyl, or pyridyl or pyrimidyl; or C and D together with the nitrogen atom to which they are attached may contain one or two double bonds or one further nitrogen, oxygen or sulfur atom. forming a 5- or 6-membered ring which may contain and which may be substituted by 1 to 3 identical or different substituents from the group consisting of methyl, ethyl, methylcarbonyl and ethylcarbonyl; , X is hydrogen, fluorine, chlorine, methyl, ethyl, n- or isobrovir, methoxy, ethoxy, n- or l
- broboxy, halogenomethyl containing 1, 2 or 3 fluorine and/or chlorine atoms, halogenoethyl containing 1 to 5 fluorine and/or chlorine atoms, or in each case unsubstituted or 7enoxy or 7enylthio substituted by 1 to 5 identical or different substituents, the substituents selected for 7enyl being fluorine, chlorine, bromine, methyl, ethyl, n-
or isoprovir, methoxy, ethoxy, n- or isopropoxy and trifluoromethyl, Y represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, and 2 represents fluorine or chlorine; n represents the number 0, l, 2 or 3, and A is methyl, ethyl, in each case linear or branched globil, butyl, bentyl, hexyl, heptyl, octyl,
nonyl or decyl, halogeno C+Ca-alkyl, C S- C ,-alganyl, C. -C,-alkynyl, C. -C,-alkoxyC,-C,-alkyl or C,-C4-alkylthioC,-C4-
represents alkyl or represents cycloalkyl having 3 to 6 ring atoms, which may be interrupted by oxygen, nitrogen and/or sulfur, or A is in each case unsubstituted or 1 to 5 ring atoms; It particularly represents phenyl, benzyl or 7enethyl substituted by l to 3 identical or different substituents, the substituents selected in each case being fluorine, chlorine, methyl, ethyl, n- or isoprobyl, methoxy, ethoxy , trifluoromethyl, tri7fluoromethoxy or in each case unreplaced or selected from the group consisting of fluorine, chlorine, methyl, methoxy, trifluoromethyl and trifluoromethoxy.
4-alkoxy and 4-(substituted) of formula (I) of l above selected from 7-enoxy or 7-enylthio substituted with 3 identical or different substituents;
Amino-3-arynorevirorinone derivatives. 5. General formula (I) [wherein X and Y independently of each other represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, or in each case unsubstituted or substituted aryloxy or arylthio, Z is halogen, represents alkyl or alkoxy, n represents the number 0, 1, 2 or 3, A is in each case unsubstituted or in each case haloken-substituted anolequinole, anolekenynole, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl , unsubstituted or arylalkyl substituted by halogen, alkyl, halogenoalkyl, alkoxy and/or nitro, or unsubstituted or substituted aryl, optionally interrupted by a petero atom; Possible substituents here are halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or phenoxy or phenylthio, in each case unsubstituted or substituted by halogen, alkyl, alkoxy, halogenoalkyl and/or halogenoalkoxy, B represents hydroxyl, alkoxy, halogenoalkoxy or cycloalkoxy, the cycloalkyl group being unsubstituted or substituted by halogen and/or alkyl, or D C and D independently of each other represent hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, cycloalkyl optionally interrupted by a heteroatom I, or in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetaryl represents alkyl or C and D together with the nitrogen atom to which they are attached are optionally substituted, optionally interrupted by other heteroatoms of 3 to 9 members; with the proviso that if B represents hydroxyl and A has a meaning other than optionally substituted aryl, at least one group X, Y or 2 is does not represent chlorine or methyl] 4-alkoxy and 4-(substituted) amino-3-arylpyrrolinone derivatives of The compound of formula (I) having the formula (
II) [wherein A, X1Y%Z and n have the above meanings, and R
b) B is alkoxy, Compounds of formula (I) representing halogenoalkoxy or cycloalkoxy, the cycloalkyl group being unsubstituted or substituted by halogen and/or alkyl, and A1x, y, z and n having the abovementioned meanings is a compound of formula (I) in which B represents hydroxyl, optionally in the presence of a diluent and optionally in the presence of an acid-binding agent, to form a compound of formula (II[) R2 represents alkyl or cycloalkyl, the cycloalkyl group being unsubstituted or substituted by halogen and/or alkyl, and X1 represents halogen or another radical common for alkylating reagents. or C) a compound of formula (I) in which B represents N and \DA, C, DSX, Y%2 and n have the meanings given above, represents hydroxyl (I
) with amines of the formula (IV) C/HN (IV)\DE where C8 and D have the meanings given above, optionally in the presence of a diluent and optionally a dehydrating agent. A method characterized by causing 6. A herbicide characterized by containing at least one 4-alkoxy and 4-(substituted) amino-3-arylvirolinone derivative of formula (I) of formulas 1 to 5 above. 7. 4-alkoxy of formula (I) of above 1 to 5 and 4
- A method for controlling undesirable plants, characterized by applying (substituted) amino-3-arylvirolinone derivatives to plants and/or their environment. 8. Use of 4-alkoxy and 4-(It-substituted)amino-3-arylpyrrolinone derivatives of formula (I) according to 1 to 5 above for controlling undesirable plants. 9. 4-alkoxy and 4 of formula (1) in 1 to 5 above
- A process for the production of herbicides, characterized by mixing (substituted) amino-3-arylvirolinone derivatives with extenders and/or surface-active substances.

Claims (1)

[Claims] 1. General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) [In the formula, X and Y are independently hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, or In each case represents unsubstituted or substituted aryloxy or arylthio, Z represents halogen, alkyl or alkoxy, n represents the number 0, 1, 2 or 3, A is in each case unsubstituted or each Halogen in both cases
substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, cycloalkyl optionally interrupted by a heteroatom, unsubstituted or halogen,
represents arylalkyl substituted by alkyl, halogenoalkyl, alkoxy and/or nitro, or unsubstituted or substituted aryl, in which the possible substituents are halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or in each case Both are phenoxy or phenylthio, which is unsubstituted or substituted by halogen, alkyl, alkoxy, halogenoalkyl and/or halogenoalkoxy, and B represents hydroxyl, alkoxy, halogenoalkoxy or cycloalkoxy, and the cycloalkyl group is unsubstituted. or substituted by halogen and/or alkyl, or B represents a group ▲formula, chemical formula, table etc.▼, where C and D independently of each other are hydrogen, alkyl, alkenyl, alkoxyalkyl , alkylthioalkyl or polyalkoxyalkyl, cycloalkyl optionally interrupted by a heteroatom, or in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl, or C and D together with the nitrogen atom to which they are attached form a 3- to 9-membered optionally substituted ring optionally interrupted by other heteroatoms; provided that if B represents hydroxyl and A has a meaning other than optionally substituted aryl, at least one group X, Y or Z does not represent chlorine or methyl] 4-alkoxy- and 4-(substituted) amino-
3-Arylpyrrolinone derivatives. 2. General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, X and Y are each independently hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, or unsubstituted or substituted aryloxy or arylthio, Z represents halogen, alkyl or alkoxy, n represents the number 0, 1, 2 or 3, A is in each case unsubstituted or in each case halogen-
substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, cycloalkyl optionally interrupted by a heteroatom, unsubstituted or halogen,
represents arylalkyl substituted by alkyl, halogenoalkyl, alkoxy and/or nitro, or unsubstituted or substituted aryl, in which the possible substituents are halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or in each case Both are phenoxy or phenylthio, which is unsubstituted or substituted by halogen, alkyl, alkoxy, halogenoalkyl and/or halogenoalkoxy, and B represents hydroxyl, alkoxy, halogenoalkoxy or cycloalkoxy, and the cycloalkyl group is unsubstituted. or substituted by halogen and/or alkyl, or B represents a group ▲formula, chemical formula, table etc.▼, where C and D independently of each other are hydrogen, alkyl, alkenyl, alkoxyalkyl , alkylthioalkyl or polyalkoxyalkyl, cycloalkyl optionally interrupted by a heteroatom, or in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl, or C and D together with the nitrogen atom to which they are attached form a 3- to 9-membered optionally substituted ring optionally interrupted by other heteroatoms; provided that if B represents hydroxyl and A has a meaning other than optionally substituted aryl, at least one group X, Y or Z does not represent chlorine or methyl] 4-alkoxy- and 4-(substituted) amino-
In the method for producing 3-arylpyrrolinone derivatives, a) a compound of formula (I) in which B represents hydroxyl and groups A, X, Y and Zn have the above meanings is a compound of formula (II) ▲mathematical formula, chemical formula , tables, etc.▼(II) [In the formula, L A, X, Y, Z and n have the above meanings, and R
^1 represents alkyl, in particular methyl or ethyl] or b) B is alkoxy , halogenoalkoxy or cycloalkoxy, the cycloalkyl group being unsubstituted or substituted by halogen and/or alkyl, and A, X, Y, Z and n having the abovementioned meanings ) is a compound of formula (I) in which B represents hydroxyl, optionally in the presence of a diluent and optionally in the presence of an acid-binding agent, to form a compound of formula (III) R^2-X^1(III) [formula where R^2 represents alkyl, halogenoalkyl or cycloalkyl, the cycloalkyl group being unsubstituted or substituted by halogen and/or alkyl, and X^1 being halogen or for the alkylating reagent. representing another general leaving group], or c) B represents ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
and a compound of formula (I) in which A, C, D, X, Y, Z and n have the above meanings is a compound of formula (I) in which B represents hydroxyl;
I) in the presence of an appropriate diluent and an appropriate dehydrating agent to obtain the formula (IV) ▲Mathematical formula, chemical formula, table, etc.▼(IV) [wherein C and D have the above meanings] ] A method characterized by reacting with amines. 3. At least one type of formula (
Herbicides characterized by containing the 4-alkoxy- and 4-(substituted) amino-3-arylpyrrolinon derivatives of I). 4. 4-alkoxy- and 4-alkoxy of formula (I) according to claim 1 for controlling undesirable plants
- Use of (substituted) amino-3-arylpyrrolinone derivatives.